7-hydroxy-3-(4-hydroxyphenyl)-8-[(3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one

• ChemBase ID: 179896
• Molecular Formular: C21H20O9
• Molecular Mass: 416.3781
• Monoisotopic Mass: 416.11073222
• SMILES: c12c(C3O[C@@H]([C@H]([C@@H]([C@H]3O)O)O)CO)c(ccc1c(=O)c(co2)c1ccc(cc1)O)O
• Canonical SMILES: OC[C@H]1OC([C@@H]([C@H]([C@@H]1O)O)O)c1c(O)ccc2c1occ(c2=O)c1ccc(cc1)O
• InChI: InChI=1S/C21H20O9/c22-7-14-17(26)18(27)19(28)21(30-14)15-13(24)6-5-11-16(25)12(8-29-20(11)15)9-1-3-10(23)4-2-9/h1-6,8,14,17-19,21-24,26-28H,7H2/t14-,17-,18+,19-,21?/m1/s1
• InChIKey: HKEAFJYKMMKDOR-YWFAZRBLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-hydroxy-3-(4-hydroxyphenyl)-8-[(3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one
• IUPAC Traditional name: 7-hydroxy-3-(4-hydroxyphenyl)-8-[(3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one
• Synonyms: 8--D-Glucopyranosyl-7-hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; 8--D-Glucopyranosyl-4',7-dihydroxyisoflavone; Daidzein 8-C-glucoside; 8-Glucopyranosyldaidzein; 8-Glucosyldaidzein; Puerarin

Database IDs

• CAS Number: 3681-99-0
• PubChem SID: 164235806
• PubChem CID: 5486172

CALCULATED PROPERTIES

• Acid pKa: 6.0298758
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -0.13829933
• LogD (pH = 7.4): -1.3562676
• Log P: -0.026883194
• Molar Refractivity: 102.8203 cm^3
• Polarizability: 40.101902 Å^3
• Polar Surface Area: 156.91 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Possesses -adrenergic receptor blocking props.

Product Information

• Biological Source: Isol. from Pueraria spp.
• Application(s): Puerarin is a drug that has self-microemulsifying drug delivery system researches going on

REFERENCES

• Shi, H. P; S. Kintzies (2003). "Genetic transformation of Pueraria phaseoloides with Agrobacterium rhizogenes and puerarin production in hairy roots". Plant Cell Reports (Springer) 21 (11): 1103?107
• Pharmacology, biochemistry, and behavior 75 (3)
• Wang, Lingzhao et al. (2009). "Investigation of supercritical fluid extraction of puerarin from Pueraria Lobata". Journal of Food Process Engineering (John Wiley & Sons) 32 (5)
• Overstreet DH, Kralic JE, Morrow AL, Ma ZZ, Zhang YW, Lee DY (2003). "NPI-031G (puerarin) reduces anxiogenic effects of alcohol withdrawal or benzodiazepine inverse or 5-HT2C agonists.".
• Chen, Gang et al. (2001). "Determination of puerarin, daidzein and rutin in Pueraria lobata (Wild.) Ohwi by capillary electrophoresis with electrochemical detection".
• Journal of Chromatography A (Elsevier) 923 (1 - 2)
• Kintzios, Spiridon et al. (2004). "Scale-up production of puerarin from hairy roots of Pueraria phaseoloides in an airlift bioreactor". Biotechnology Letters (Springer) 26 (13): 1057?059.